By employing the natural product quinic acid as starting material, a series of synthetic small molecule macrolides reminiscent of the cell migration inhibitor migrastatin were synthesized and characterized as antibiotics and tumor cell migration inhibitors. Three of the macrolides were shown to inhibit 4T1 breast cancer cell migration with low nanomolar to sub-micromolar IC50 values (ranging from 70-500 nM) in complementary assays including a quantitative cell migration assay and a semiquantitative wound healing assay. In a separate study, a quinic acid scaffold was used to build a small library of mycothiol analogs and shown to be low to sub-micromolar inhibitors of the mycobacterium detoxification enzyme mycothiol-S-conjugate amidase. Structural studies on natural product and natural product-like inhibitors of mycobacterial enzymes are ongoing.